Imidamide derivatives

ABSTRACT

The present invention relates to novel imidamide derivatives of the formula (I)in whichR, R&lt;1&gt;, R&lt;2 &gt;and R&lt;3 &gt;are each as defined in the description, to a process for their preparation and to their use for controlling animal pests, such as insects, arachnids and, in particular, nematodes.

This application is a 371 of PCT/EP99/04747, filed Jul. 7, 1999.

The present invention relates to novel imidamide derivatives, to aprocess for their preparation and to their use for controlling animalpests.

Certain imidamide derivatives are already known (cf. WO 91 04 965, WO 9304 032, EP 0 403 159; J. Organomet. Chem. (1975), 97 (1), pp. 39-44;Bull. Soc. Chim. Belg. (1981), 90 (1), pp. 89-98). The insecticidalproperties of some of these compounds have also been known.

This invention provides novel imidamide derivatives of the generalformula (I)

in which

R represents cyano or nitro,

R¹ represents hydrogen, optionally substituted alkyl, optionallysubstituted cycloalkyl or optionally substituted phenyl,

R² represents hydrogen, optionally substituted alkyl or optionallysubstituted cycloalkyl and

R³ represents the groupings

 where

R⁴ and R⁵ independently of one another each represent hydrogen,optionally substituted alkyl or optionally substituted cycloalkyl,

R⁶ and R⁷ independently of one another represent optionally substitutedaryl, optionally substituted cycloalkyl or represent an optionallysubstituted mono- or bicyclic, nitrogen-free heterocycle.

R⁸ represents alkyl or optionally substituted aryl,

X represents a single bond, represents in each case straight-chain orbranched alkanediyl, alkenediyl, alkinediyl and also represents thegroupings —A—O—, —A—S—, —A—O—A′-, —A—S—A′—, —A—N(Alk)- or —A—N(Alk)-A′—,where the moiety A is attached to the C atom of the grouping—C(R⁴R⁵)—X—R⁶;

Alk represents alkyl and

A and A′ independently of one another each represent straight-chain orbranched alkanediyl and

Y represents a single bond and also the groupings —O—A—, —O—A″—O—,—O—A″—S—, —O—A″—SO—, —O—A″—SO₂—, —O—A″—O—A′— or —O—A″—S—A′—, where the Oatom of these groupings is always attached to the N atom of the skeletonof the formula (I):

A and A′ are each as defined above and

A″ represents straight-chain or branched alkanediyl having it least 2carbon atoms between the heteroatoms.

with the proviso that for R=CN and R²=H the compounds in which

are excluded.

Depending, inter alia, on the substituents, the imidamide derivatives ofthe formula (I) may be present as optical and/or geometrical isomers.The present invention relates both to the various isomer mixtures and tothe pure isomers.

The novel imidamide derivatives of the general formula (I) are obtainedwhen ethaneimido esters of the formula (II)

in which

R and R¹ are each as defined above,

Q represents oxygen or sulphur and

Z represents alkyl

are reacted with amines of the formula (III)

in which

R² and R³ are each as defined above

in the presence of a diluent.

The novel imidamide derivatives of the general formula (I) havepronounced biological properties and are suitable in particular forcontrolling animal pests, such as insects, arachnids and, in particular,nematodes encountered in agriculture, in forests, in the protection ofstored products and materials and in the hygiene sector.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below.

R preferably represents cyano or nitro.

R¹ preferably represents hydrogen, represents optionally halogen-,cyano- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, representsC₃-C₆-cycloalkyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen C₁-C₄-alkyl or represents phenol which is optionally mono- totrisubstitued by identical or different substituents, possiblesubstituents being the phenyl substituents mentioned under R⁶.

R² preferably represents hydrogen, represents optionally halogen-,cyano- or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl or representsC₃-C₆-cycloalkyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen or C₁-C₄-alkyl;

R³ preferably represents the groupings

 where

R⁴ and R⁵ independently of one another each preferably representhydrogen, represent optionally halogen-, cyano- orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl or represent C₃-C₆-cycloalkyl whichis optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen orC₁-C₄-alkyl.

R⁶ and R⁷ independently of one another each preferably represent phenyl,naphthyl, dihydronaphthyl and tetrahydronaphthyl, each of which isoptionally mono- to pentasubstituted by identical or differentsubstituents, possible substituents being those below:

hydroxyl, amino, cyano, nitro, halogen; in each case optionallyhydroxyl-, cyano- or halogen-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkylamino and di-(C₁-C₄-alkyl)amino; in each case optionallyhalogen-substituted C₁-C₄-alkyl-carbonyl, C₁-C₄-alkoxy-carbonyl,C₁-C₄-alkyl-carbonyl-amino, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl andC₁-C₄-alkylsulphonyl, aminocarbonyl, aminothiocarbonyl,C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)amino-carbonyl,amino-sulphonyl, C₁-C₄-alkylaminosulphonyl anddi-(C₁-C₄-alkyl)amino-sulphonyl; and also phenyl, phenoxy, phenylthio,phenylsulphinyl, phenylsulphonyl, benzyl and phenylamino, each of whichis optionally substituted by hydroxyl, cyano, nitro, halogen,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl and C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl andC₁-C₄-halogenoalkylsulphonyl having in each case 1 to 5 identical ordifferent halogen atoms from the series consisting of chlorine, fluorineand bromine;

furthermore represent C₃-C₁₂-cycloalkyl or C₅-C₁₂-cycloalkenyl, each ofwhich is optionally mono- to pentasubstituted by identical or differentsubstituents, possible substituents being:

Halogen, optionally substituted C₁-C₄-alkyl, preferred substituentsbeing: halogen, such as fluorine, chlorine, bromine, optionallysubstituted C₂-C₆-cycloalkyl and optionally substituted phenyl;

furthermore C₁-C₄-alkyl, C₁-C₄-alkoxy and also C₁-C₄-halogenoalkyl andC₁-C₄-halogenoalkoxy having in each case 1to 5 identical or differenthalogen atoms selected from the series consisting of fluorine, chlorineand bromine;

and also represent a saturated or partially unsaturated or unsaturatedmono-, bi- or tricyclic nitrogen-free heterocycle having 4 to 10 C atomsand 1to 3 identical or different heteroatoms, such as O and S atoms,which is optionally mono- to pentasubstituted by identical or differentsubstituents, possible substituents being the phenyl substituentsmentioned under R⁶.

R⁸ preferably represents C₁-C₄-alkyl or represents phenyl and naphthyl,each of which is optionally mono- to pentasubstituted by identical ordifferent substituents, possible substituents being the phenylsubstituents mentioned under R⁶.

X preferably represents a single bond, represents in each casestraight-chain or branched C₁-C₆-alkanediyl, C₂-C₆-alkenediyl orC₂-C₆-alkinediyl and also represents the groupings —A—O—, —A—S—,—A—O—A′—, —A—S—A′—, —A—N(Alk)- or —A—N(Alk)-A′—,

where

Alk preferably represents C₁-C₄-alkyl and

A and A′ independently of one another each preferably representstraight-chain or branched C₁-C₆-alkanediyl.

Y preferably represents a single bond and also the groupings —O—A—,—O—A″—O—, —O—A″—S—, —O—A″—SO—, —O—A″—SO₂—, —O—A″—O—A′— or —O—A″—S—A′—,where

A and A′ are each preferably as defined above.

A″ preferably represents straight-chain or branched C₂-C₄-alkanediylhaving at least 2 carbon atoms between the heteroatoms.

The preferred definitions are given with the proviso that for R=CN andR²=H the compounds in which

are excluded.

R particularly preferably represents cyano or nitro.

R¹ particularly preferably represents hydrogen, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or, ethoxy-substitutedmethyl, ethyl, n- or i-propyl and n- i-, s- or t-butyl; representscyclopropyl, cyclopentyl and cyclohexyl, each of which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine, methyl andethyl or represents phenyl which is optionally mono- to trisubstitutedby identical or different substituents, possible substituents being thephenyl substituents mentioned under R⁶.

R² particularly preferably represents hydrogen, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl, or representscyclopropyl, cyclopentyl and cyclohexyl, each of which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine, methyl andethyl.

R³ particularly preferably represents the groupings

 where

R⁴ and R⁵ independently of one another each particularly preferablyrepresent hydrogen, represent in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyland n-, i-, s- or t-butyl, or represent cyclopropyl, cyclopentyl andcyclohexyl, each of which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl and ethyl.

R⁶ and R⁷ independently of one another each particularly preferablyrepresent phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl, eachof which is optionally mono- to trisubstituted by identical or differentsubstituents, possible substituents being:

cyano, nitro, amino, fluorine, chlorine, bromine; in each caseoptionally fluorine- or chlorine-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-,i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino ordimethylamino; in each case optionally fluorine- and/orchlorine-substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,n- or i-propoxycarbonyl, methylthio, methylsulphinyl, methylsulphonyl,ethylthio, ethylsulphinyl or ethylsulphonyl; aminocarbonyl,aminothiocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- ori-propylaminocarbonyl, dimethylaminocarbonyl, diethyl aminocarbonyl,aminosulphonyl, methylaminosulphonyl, ethylaminosulphonyl,dimethylaminosulphonyl and diethylaminosulphonyl;

and also in each case optionally cyano-, nitro-, fluorine-, chlorine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethioxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethlylsulphinyl, n-or i-propylsulphinl-, methylsulphonyl-, ethylsulphonyl-, n- ori-propylsulphonyl-, difluoromethoxy- or trifluoromethoxy-,trifluoromethylthio-, trifluoromethylsulphinyl- ortrifluoromethylsulphonyl-substituted phenyl, phenoxy, phenylthio,phenylsulphinyl, phenylsulphonyl, benzyl or phenylamino;

furthermore represent cyclopentane, cyclohexane, cyclopentene andcyclohexene, each of which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, methyl, ethyl, n- or i-propyl, optionallysubstituted cyclohexyl-C₁-C₄-alkyl, optionally substitutedphenyl-C₁-C₄-alkyl, methoxy, ethoxy, trifluoromethyl andtrifluoromethoxy;

and also represent a saturated or partially unsaturated or unsaturatedmono- or bicyclic nitrogen-free heterocycle having 4 to 9 C atoms and 1to 3 identical or different heteroatoms, such as O and S atoms, which isoptionally mono- to pentasubstituted by identical or differentsubstituents, possible substituents being:

cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy,trifluoromethylthio and dimethylamino.

R⁸ particularly preferably represents methyl, ethyl, n- or i-propyl; n-,i-, s- or t-butyl or represents phenyl which is optionally mono- totrisubstituted by identical or different substituents, possiblesubstituents being the phenyl substituents mentioned under R⁶.

X particularly preferably represents a single bond and also representsthe groupings: —CH)₂—, —(CH₂)₂—, —(CH₂)₃—, —(CH₂)₄—, —H(CH₃)—,—CH(C₂H₅)—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CH(CH₃)CH₂CH₂—, —C(CH₃)₂—,—CH₂C(CH₃)₂—, —CH₂CH(C₃)CH₂—, —CH(CH₃)—CH(CH₃)—, —CH(C₂H₅)CH₂CH₂—;—CH₂O—, —CH₂S—, —(CH₂)₂O—, —(CH₂)₂S—, —CH(CH₃)CH₂O—, —CH(C₂H₅)CH₂O—;—CH₂OCH₂—, CH₂SCH₂—, —CH(CH₃)CH₂OCH₂—, —CH(C₂H₅)CH₂OCH₂—; —CH═CH—,—C(CH₃)═CH, —CH₂—CH═CH—, —CH₂—C(CH₃)═CH—, —C≡C—, —CH₂—C≡C—,—CH(CH₃)—C≡C—; —CH₂—N(CH₃)—, —(CH₂)₂—N(CH₃)—, —(CH₂)₃—N(CH₃)—,—CH₂—N(C₂H₅)—, —(CH₂)₂—N(C₂H₅)—, —(CH₂)₃—N(C₂H₅)—, —CH₂—N(CH₃)—CH₂—,—(CH₂)₂—N(CH₃)—CH₂—, —(CH₂)₃—N(CH₃)—CH₂—, —CH₂—N(C₂H₅)—CH₂—,—(CH₂)₂—N(C₂H₅)—CH₂—, —(CH₂)₃—N(C₂H₅)—CH₂—.

Y particularly preferably represents a single bond and also representsthe groupings —OCH₂—, —O(CH₂)₂—, —O(CH₂)₃—, —O(CH₂)₄—, —OCH(CH₃)—,—OCH(C₂H₅)—, —OCH(CH₃)CH₂—, —OCH₂CH(CH₃)—, —OCH(C₂H₅)CH₂—,—OCH(CH₃)CH₂CH₂—, —OCH(C₂H₅)CH₂CH₂—, —OCH₂CH(CH₃)CH₂—, —OCH₂CH₂CH(CH₃)—,—OCH₂CH₂O—, —OCH₂CH₂S—, —OCH₂CH₂SO—, —OCH₂CH₂SO₂—, —OCH(CH₃)CH₂O—,—OCH(C₂H₅)CH₂O—, —OCH(CH₃)CH₂S—, —OCH(C₂H₅)CH₂S—, —OCH₂CH₂OCH₂—,—OCH₂CH₂SCH₂—, —OCH(CH₃)CH₂OCH₂—, —OCH(CH₃)CH₂SCH₂—, —OCH(C₂H₅)CH₂OCH₂—,—OCH(C₂H₅)CH₂SCH₂—.

The particularly preferred definitions are given with the proviso thatfor R=CN and R²=H the compounds in which

are excluded.

R very particularly preferably represents cyano or nitro.

R¹ very particularly preferably represents hydrogen, methyl, ethyl, n-or i-propyl, cyclopropyl or phenyl.

R² very particularly preferably represents hydrogen, methyl, ethyl, n-or i-propyl or cyclopropyl.

R³ very particularly preferably represents the groupings

 where

R⁴ and R⁵ independently of one another each very particularly preferablyrepresent hydrogen, methyl ethyl, n- or i-propyl and also cyclopropyl.

R⁶ and R⁷ independently of one another each very particularly preferablyrepresent phenyl or naphthyl, each of which is optionally mono- totrisubstituted by identical or different substituents, possiblesubstituents being:

cyano, nitro, amino, fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,trifluoromethyl, difluoromethyl, trifluoromethoxy, difuoromethoxy,trifluoromethylthio, methylamino, dimethylamino, acetyl, propionyl,methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulphinyl,methylsulphonyl, methylaminocarbonyl, ethylaminocarbonyl, n- ori-propylaminocarbonyl, dimethylaminocarbonyl and diethylaminocarbonyl;and also in each case optionally cyano-, nitro-, fluorine-, chlorine-,methyl-, methoxy-, methylthio-, methylsulphinyl-, methylsulphonyl-,trifluoromethyl- or trifluoromethoxy-, trifluoromethylthio-,trifluoromethylsulphinyl- or trifluoromethylsulphonyl-substitutedphenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, benzyl orphenylamino;

furthermore represent cyclopentane or cyclohexane, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,methyl, ethyl, i-propyl, methoxy, ethoxy, trifluoromethyl andtrifluoromethoxy;

and also represent the following heterocycles which are optionally mono-to pentasubstituted by identical or different substituents:

possible (additional) substituents being:

cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, methoxy, trifluoromethyl or dimethylamino or optionallysubstituted phenyl, the possible substituents for the phenyl radicalbeing the substituents which have also been mentioned under R⁶ for thephenyl radical.

R⁸ very particularly preferably represents methyl, ethyl, n- ori-propyl; n-, i-, s- or t-butyl or represents phenyl which is optionallymono- to trisubstituted by identical or different substituents, possiblesubstituents being the phenyl substituents mentioned under R⁶.

X very particularly preferably represents a single bond and alsorepresents the groupings, —CH₂—, —(CH₂)₂—, —(CH₂)₃—, —CH(CH₃)—,—C(CH₃)₂—, —CH₂C(CH₃)₂—, —CH(CH₃)CH₂—, —CH₂—, —CH₂S—, —(CH₂)₂O—,—(CH₂)₂S—, —CH₂OCH₂—, CH₂SCH₂—, —C(CH₃)═CH, —C≡C—, —(CH₂)₃—N(CH₃)—,—(CH₂)₃—N(C₂H₅)—, —(CH₂)₃—N(CH₃)—CH₂—, —(CH₂ )₃—N(C₂H₅)—CH₂—.

Y very particularly preferably represents a single bond and alsorepresents the groupings —OCH₂—, —O(CH₂)₂—, —O(CH₂)₃—, —O(CH₂)₄—,—OCH(CH₃)—, —OCH(C₂H₅)—, —OCH(CH₃)CH₂—, —OCH(CH₃)CH₂CH₂—,—OCH(C₂H₅)CH₂CH₂—, —OCH₂CH₂O—, —OCH₂CH₂S—, —OCH₂CH₂SO—, —OCH₂CH₂SO₂—,—OCH(CH₃)CH₂O—, —OCH(C₂H₅)CH₂O—, —OCH(CH₃)CH₂S—, —OCH(C₂H₅)CH₂S—,—OCH₂CH₂OCH₂—, —OCH₂CH₂SCH₂—.

The very particularly preferred definitions are given with the provisothat for R=CN and R²=H the compounds in which

are excluded.

Preferred compounds according to the invention are substances of theformulae (Ia) to (Ih):

in which

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, X and Y each have the general,preferred, particularly preferred and very particularly preferredmeanings mentioned above.

Particular emphasis is here given to the compounds of the above formula(Ib).

Preferred compounds according to the invention are also substances ofthe formulae (IA) to (IW):

in which

R³, R⁴, R⁵ and R⁶ each have the general, preferred, particularlypreferred and very particularly preferred meanings mentioned above.

Preferred compounds according to the invention are furthermoresubstances of the formulae (I-1) to (I-56)

in which

R¹, R², R⁶ and R⁷ each have the general; preferred, particularlypreferred and very particularly preferred meanings mentioned above.

The abovementioned general or preferred radical definitions orillustrations apply both to the end products and, correspondingly, tothe starting materials and intermediates. These radical definitions canbe combined with each other as desired, i.e. including combinationsbetween the respective preferred ranges.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings mentioned aboveas being preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningsgiven above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

In the radical definitions listed above and below, hydrocarbon radicals,such as alkyl or alkenyl, are in each case straight-chain or branched asfar as this is possible—also in combination with heteroatoms, such as inalkoxy or alkylthio.

Specifically, the following compounds may be mentioned:

TABLE 1 (Ib)

Compounds of Table 1 correspond to the general formula (Ib), in which

R¹=CH₃

R²=H

C(R⁴,R⁵)=CH₂

XR⁶=as listed below:

XR⁶

Table 2

Compounds of Table 2 correspond to the general formula (Ib) in which

C(R⁴,R⁵)=CH(CH₃)

R¹, R² and XR⁶=as listed in Table 1.

Table 3

Compounds of Table 3 correspond to the general formula (Ib) in which

C(R⁴,R⁵)=CH(C₂H₅)

R¹, R² and XR⁶=as listed in Table 1.

Table 4

Compounds of Table 4 correspond to the general formula (Ib) in which

C(R⁴,R⁵)=CH(C₃H₇-i)

R¹, R² and XR⁶=as listed in Table 1.

Table 5

Compounds of Table 5 correspond to the general formula (Ib) in which

C(R⁴,R⁵)=CH(C₃H₇-n)

R¹, R² and XR⁶=as listed in Table 1.

Table 6

Compounds of Table 6 correspond to the general formula (Ib) in which

C(R⁴,R⁵)=C(CH₃)₂

R¹, R² and XR⁶=listed in Table 1.

Tables 7-12

Compounds of Tables 7-12 correspond to the general formula (Ib) in which

R¹=C₂H₅

R²=H

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 13-18

Compounds of Tables 13-18 correspond to the general formula (Ib) inwhich

R¹=C₃H₇-i

R²=H

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 19-24

Compounds of Tables 19-24 correspond to the general formula (Ib) inwhich

R¹=C₃H₇-n

R²=H

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 25-30

Compounds of Tables 25-30 correspond to the general formula (Ib) inwhich

R¹=

R²=H

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 31-36

Compounds of Tables 31-36 correspond to the general formula (Ib) inwhich

R¹=H

R²=H

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 37-42

Compounds of Tables 37-42 correspond to the general formula (Ib) inwhich

R¹=H

R²=CH₃

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 43-48

Compounds of Tables 43-48 correspond to the general formula (Ib) inwhich

R¹=H

R²=C₂H₅

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 49-54

Compounds of Tables 49-54 correspond to the general formula (Ib) inwhich

R¹=CH₃

R²=CH₃

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 55-60

Compounds of Tables 55-60 correspond to the general formula (Ib) inwhich

R¹=CH₃

R²=C₂H₅

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 61-66

Compounds of Tables 61-66 correspond to the general formula (Ib) inwhich

R¹=CH₃

R²=C₃H₇-i

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 67-72

Compounds of Tables 67-72 correspond to the general formula (Ib) inwhich

R¹=C₂H₅

R²=CH₃

C(R⁴,R⁵)=as listed in Tables 1 to 6

XR⁶=as listed in Table 1.

Tables 73-78

Compounds of Tables 73-78 correspond to the general formula (Ib) inwhich

R¹=CH₅

R²=C₂H₅

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 79-84

Compounds of Tables 79-84 correspond to the general formula (Ib) inwhich

R¹=C₃H₇-i

R²=CH₃

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 85-90

Compounds of Tables 85-90 correspond to the general formula (Ib) inwhich

R¹=C₃H₇-i

R²=C₂H₅

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 91-96

Compounds of Tables 91-96 correspond to the general formula (Ib) inwhich

R¹=C₃H₇-n

R²=CH₃

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 97-102

Compounds of Tables 97-102 correspond to the general formula (Ib) inwhich

R¹=C₃H₇-n

R²=C₂H₅

C(R⁴,R⁵)=as listed in Tables 1 to 6

XR⁶=as listed in Table 1.

Tables 103-108

Compounds of Tables 103-108 correspond to the general formula (Ib) inwhich

R¹=

R²=CH₃

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

Tables 109-114

Compounds of Tables 109-114 correspond to the general formula (Ib) inwhich

R¹=

R²=C₂H₅

C(R⁴,R⁵)=as listed in Tables 1to 6

XR⁶=as listed in Table 1.

TABLE 115 (Ic)

Compounds of Table 115 correspond to the general formula (Ic) in which

R¹=CH₃

R²=H

YR⁷=as listed below:

YR⁷

Table 116

Compounds of Table 116 correspond to the general formula (Ic) in which

R¹=C₂H₅

R²=H

YR⁷=as listed in Table 115.

Table 117

Compounds of Table 117 correspond to the general formula (Ic) in which

R¹=C₃H₇-i

R²=H

YR⁷=as listed in Table 115.

Table 118

Compounds of Table 118 correspond to the general formula (Ic) in which

R¹=C₃H₇-n

R²=H

YR⁷=as listed in Table 115.

Table 119

Compounds of Table 119 correspond to the general formula (Ic) in which

R¹=

R²=H

YR⁷=as listed in Table 115.

Table 120

Compounds of Table 120 correspond to the general formula (Ic) in which

R¹=H

R²=H

YR⁷=as listed in Table 115.

Table 121

Compounds of Table 121 correspond to the general formula (Ic) in which

R¹=H

R²=CH₃

YR⁷=as listed in Table 115.

Table 122

Compounds of Table 122 correspond to the general formula (Ic) in which

R¹=H

R²=C₂H₅

YR⁷=as listed in Table 115.

Table 123

Compounds of Table 123 correspond to the general formula (Ic) in which

R¹=H

R²=C₃H₇-i

YR⁷=as listed in Table 115.

Table 124

Compounds of Table 124 correspond to the general formula (Ic) in which

R¹=CH₃

R²=CH₃

YR⁷=as listed in Table 115.

Table 125

Compounds of Table 125 correspond to the general formula (Ic) in which

R¹=CH₃

R²=C₂H₅

YR⁷=as listed in Table 115.

Table 126

Compounds of Table 126 correspond to the general formula (Ic) in which

R¹=CH₃

R²=C₃H₇-i

YR⁷ as listed in Table 115.

Table 127

Compounds of Table 127 correspond to the general formula (Ic) in which

R¹=C₂H₅

R²=CH₃

YR⁷=as listed in Table 115.

Table 128

Compounds of Table 128 correspond to the general formula (Ic) in which

R¹=C₂H₅

R²=C₂H₅

YR⁷=as listed in Table 115.

Table 129

Compounds of Table 129 correspond to the general formula (Ic) in which

R¹=C₃H₇-i

R²=CH₃

YR⁷=as listed in Table 115.

Table 130

Compounds of Table 130 correspond to the general formula (Ic) in which

R¹=C₃H₇-i

R²=C₂H₅

YR⁷=as listed in Table 115.

Table 131

Compounds of Table 131 correspond to the general formula (Ic), in which

R¹=CH₃

R²=

YR⁷=as listed in Table 115.

The following compounds may be mentioned as being preferred:

TABLE a (Ib)

R¹ R² R⁴ R⁵ X R⁶ CH₃ H H CH₃ —CH₂CH₂—

CH₃ H H CH₃ —CH₂CH₂—

CH₃ H H CH₃ —CH₂CH₂—

CH₃ H H CH₃ —CH₂CH₂—

CH₃ H H CH₃ —CH₂CH₂—

CH₃ H H CH₃ —CH₂CH₂—

CH₃ H CH₃ CH₃ —CH₂CH₂—

CH₃ H CH₃ CH₃ —CH₂CH₂—

CH₃ H CH₃ CH₃ —CH₂CH₂—

CH₃ H CH₃ CH₃ —CH₂CH₂—

CH₃ H CH₃ CH₃ —CH₂CH₂—

CH₃ H CH₃ CH₃ —CH₂CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H CH₃ —CH(CH₃)CH₂—

CH₃ H H H —CH(CH₃)CH₂—

CH₃ H H H —CH(CH₃)CH₂—

CH₃ H H CH₃ —(CH₂)₃N(CH₃)—

CH₃ H H CH₃ —(CH₂)₃N(C₂H₅)—

CH₃ H H H —CH(CH₃)—

CH₃ H H H —CH(CH₃)—

CH₃ H H H —CH(CH₃)—

CH₃ H H H —CH(CH₃)—

CH₃ H H H —CH(CH₃)—

CH₃ H H H —CH(CH₃)—

CH₃ H H H —CH(CH₃)—

CH₃ H H H —CH(CH₃)—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H H CH₃ —

CH₃ H H CH₃ —

CH₃ H H CH₃ —

CH₃ H H CH₃ —

CH₃ H H CH₃ —

CH₃ H H n-C₃H₇ —

CH₃ H H H —C(CH₃)═CH—

CH₃ H H CH₃ —CH₂O—

CH₃ H H CH₃ —CH₂O—

CH₃ H H CH₃ —CH₂O—

CH₃ H H CH₃ —CH₂O—

CH₃ H H CH₃ —CH₂O—

CH₃ H H CH₃ —CH₂O—

CH₃ H H CH₃ —CH₂O—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H CH₃ CH₃ —C≡C—

CH₃ H H CH₃ —CH₂—

CH₃ H H CH₃ —CH₂—

TABLE b

(Ib-1) R⁶

TABLE c (Ib-2)

R⁶=as listed in Table b, and additionally

R⁶

TABLE d (Ib-3)

R⁶=as listed in Table c.

TABLE e (Ib-4)

R⁶

TABLE f (Ib-5)

R⁶=as listed in Table e.

TABLE g (Ib-6)

R⁶

TABLE h (Ic)

R¹ R² Y R⁷ CH₃ H —

The abovementioned compounds according to the invention of the variousformulae and in the individual tables can, if appropriate, be present asracemates, R or S isomers. Using, for example, methylN-cyano-ethaneimidate and 4-chloro-2-methylbenzylamine as startingmaterials, the course of the process according to the invention can berepresented by the following reaction scheme:

The formula (II) provides a general definition of the ethaneamido estersrequired as starting materials for carrying out the process according tothe invention. In this formula, Z preferably represents C₁-C₄-alkyl,such as, in particular, methyl or ethyl.

Most of the N-cyano-ethaneamido esters are known (cf., for example, U.S.Pat. No. 5,304,566 or J. Org. Chem. 28, 1963, 1816-1821) and/or they canbe obtained by a customary process.

The N-nitro-ethaneamido esters are obtained, for example, by nitratingthe corresponding NO₂-free ethaneamidoesters of the formula (II) in acustomary manner.

The amines of the general formula (III) further to be used as startingmaterials in the process according to the invention are generally knowncompounds of organic chemistry, and/or they can be obtained in agenerally known manner.

The process according to the invention is preferably carried out in thepresence of a diluent. Preference is given to using alcohols, such asmethanol and ethanol; nitriles, such as acetonitrile, or esters, such asethyl acetate. It is also possible, if appropriate, to carry out theprocess in water or organic-aqueous mixtures.

When carrying out the process according to the invention, the compoundsare preferably employed in equimolar amounts; however, it is alsopossible to employ an excess of one or the other starting material.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures between 0° C. and 100° C.,preferably between 20° C. and 80° C.

Work-up and isolation of the end products is carried out in a generallyknown manner.

The active compounds, while being well-tolerated by plants, and havingfavourable homeotherm toxicity, are suitable for controlling animalpests, in particular insects, arachnids and nematodes, encountered inagriculture, in forests, in the protection of stored products and ofmaterials, and in the hygiene sector. They can preferably be employed ascrop protection agents. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of Isopoda, for example, Oniscus asellus, Armadillidiumvulgare and Porcellio scaber.

From the order of Diplopoda, for example, Blaniulus guttulatus.

From the order of Clilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of Symphyla, for example, Scutigerella immiculata.

From the order of Thysanura, for example, Lepisma saccharina.

From the order of Collembola, for example, Onychitirus armatus.

From the order of Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of Blattaria, for example, Blatta orientalis, Periplanetaamericana, Leucophaea maderae and Blattella germanica.

From the order of Dermaptera, for example, Forficula auricularia.

From the order of Isoptera, for example, Reticulitermes spp.

From the order of Phthiraptera, for example, Pediculus humanus corporis,Haematopinus spp., Linognathus spp., Trichodectes spp. and Damaliniaspp.

From the order of Thysanoptera, for example, Hercinothrips femoralis,Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of Heteroptera, for example, Eurygaster spp., Dysdercusintermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus andTriatoma spp.

From the order of Homoptera, for example, Aleurodes brassicae, Bemisiatabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiclla aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of Lepidoptera, for example, Pectinophora gossypiella,Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella,Hyponomeuta padella, Plutella xylustella, Malacosoma neustria, Euproctischrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistiscitrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana,Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit. Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of Acarina, for example, Acarus siro, Argas spp.,Omrithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similtis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp, and Bursa phelenchusspp.

The compounds of the formula (I) according to the invention aredistinguished in particular by good nematicidal activity. Thus, they canbe employed particularly successfully for controlling, for example,Meloidogyne incognita.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and very fine capsules and polymeric substances.

At the appropriate application rates, Some of the compounds according tothe invention have herbicidal activity.

These formulations are prepared in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, if appropriate with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatics, such as xylene, toluene, or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzene, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane, or paraffins, for example mineral oilfractions, mineral or vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andalso water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montinorillonite ordiatomaceous earth, and ground synthetic minerals, such as finelydivided silica, alumina and silicates; suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, as well as syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;suitable emulsifiers and/or foam-formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates and proteinhydrolysates: suitable dispersants are: for example linin-sulphite wasteliquors and methycellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas and substances produced bymicroorganisms, inter alia.

Examples of particularly advantageous mixing components are thefollowing:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichiamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxylmino)-N-methyl-2-phenoxy-phenylacetamide,

isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanoneO-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropane-carboxamide.

2,6-dichloro-5-(methylthio)-4-pyrinidinyl-thiocyanate,

2,6-dichloro-N(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glycopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,

3,5-dichloro-N-[cyano-[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4,5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyloxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

ethyl[(4-chlorophenyl)-azo]-cyanoacetate,

potassium hydrogen carbonate,

methanetetrathiol sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dinmethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyidithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, AC303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlortluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpiopathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivermectin,

lambda-cyhalothrin, lufenuron,

malathion, inecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen, quinalphos,

RH 5992

salithion, sebufos, silafluofen, sulfotep, suiprofos, spinosad,

tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb, thiamethoxam.

vamidothion, XMC, xylycarb, YI 5301/5302, zetamethirin.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth-regulating substances.

When used as insecticides and nematicides, the active compoundsaccording to the invention can furthermore be present in theircommercial formulations and in the use forms prepared from theseformulations, as a mixture with synergists. Synergists are compoundswhich increase the activity of the active compounds, without it beingnecessary for the added synergist to be active itself.

The active compound content of the use forms prepared from thecommercial formulations can vary within wide ranges. The active compoundconcentration of the use form can be from 0.0000001 to 95% by weight ofactive compound, and is preferably between 0.00001 and 1% by weight.

The application is carried out in a manner which is adapted to the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by excellent residual activity on wood andclay, and by good stability to alkali on limed substrates.

At the appropriate application rates, the compounds according to theinvention also have herbicidal properties and/or growth-regulatingactivity, such as, for example, a defoliant effect.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Cuiex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaca spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohifahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyophagus spp.,Caloglyphus spp., Hypodectes spp., Perolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemioidcoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling, thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1to 80% by weight, directly or after 100 to10,000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds of the formula (I)according to the invention also have a strong insecticidal actionagainst insects which destroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis,Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis,Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.,Dinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipcs, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as

Lepisma saccarina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentsaccording to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood panelling, woodenwindows and doors, plywood, chipboard, joinery or wooden products whichare used quite generally in house-building or in building joinery.

The active compounds can be used as such, in the form of concentrates orin generally customary formulations, such as powders, granules,solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and tlimiber products comprise the active compound according tothe invention in a concentration of 0.0001 to 95% by weight, inparticular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to, employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic chemical solventor solvent mixture and/or an oily or oil-like organic chemical solventor solvent mixture of low volatility and/or a polar organic chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flash point above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flash point above 30° C., preferablyabove 45° C., can be replaced in part by organic chemical solvents ofhigh or medium volatility, providing that the solvent mixture likewisehas an evaporation number above 35 and a flash point above 30° C.,preferably above 45° C., and that the insecticide/fungicide mixture issoluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

Organic chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying coetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more, of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

Pairticularly effective prcscrvation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing components are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyiluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and also fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

The preparation and the use of the active compounds according to theinvention are illustrated by the examples below.

PREPARATION EXAMPLES Example 1

5.0 g (0.05 mol) of methyl N-cyano-ethaneimidate are added to 7.8 g(0.05 mol) of [R]-4-chloro-2-methylbenzylamine in 30 ml of methanol, andthe reaction mixture is stirred at room temperature for 2 hours. Themixture is subsequently mixed with water and the precipitate is filteredoff and dried.

This gives 7.0 g (63% of theory) of[R]-N-cyano-N′-(4-chlorophenyl-eth-1-yl)-ethaneimidamide of meltingpoint of 125° C. and with an optical rotation [α]_(D) ²⁰=+252.5°(CH₃OH).

Analogously, and/or in accordance with the general process procedures,the following compounds according to the invention are obtained:

TABLE A (Ib)

Ex. No. R¹ R² R⁴ R⁵ X R⁶ Physical const. 2 H H CH₃ H —

viscous 3 CH₃ H C₂H₅ H —

m.p. 134° C. 4 CH₃ H H CH₃ —CH₂CH₂—

m.p. 72° C. 5 CH₃ H H C₂H₅ —CH₂CH₂—

viscous 6 CH₃ H H CH₃ —CH₂CH₂—

m.p. 92° C. 7 CH₃ H H C₂H₅ —CH₂CH₂—

m.p. 90° C. 8 CH₃ H H CH₃ —CH₂CH₂—

m.p. 154° C. 9 CH₃ H H CH₃ —CH₂CH₂—

oil 10 CH₃ H H CH₃ —CH₂CH₂—

m.p. 74° C. 11 CH₃ H H n-C₃H₇ —CH₂CH₂—

n²⁰ _(D) = 1.5476 12 CH₃ H H i-C₃H₇ —CH₂CH₂—

m.p. 142° C. 13 CH₃ H H C₂H₅ —CH₂CH₂—

n²⁰ _(D) = 1.5760 14 CH₃ H H CH₃ —CH₂CH₂—

m.p. 124° C. (R isomer) 15 CH₃ H H CH₃ —CH₂CH₂—

m.p. 121° C. (S isomer) 16 CH₃ H H C₂H₅ —CH₂CH₂—

viscous 17 CH₃ H H CH₃ —

m.p. 137° C. (S isomer) 18 CH₃ H H CH₃ —CH₂CH₂—

m.p. 112° C. (R isomer) 19 CH₃ H H CH₃ —CH₂CH₂—

m.p. 140° C. (S isomer) 20 CH₃ H H C₂H₅ —CH₂CH₂—

m.p. 127° C. 21 CH₃ H H C₂H₅ —CH₂CH₂—

viscous 22 CH₃ H CH₃ CH₃ —

m.p. 135° C. 23 CH₃ H H CH₃ —

m.p. 135° C. 24 CH₃ H H C₂H₅ —

m.p. 108° C. (S isomer) 25 CH₃ H H C₂H₅ —

m.p. 117° C. (R isomer) 26 CH₃ H H i-C₃H₇ —

n²⁰ _(D) = 1.5517 27 CH₃ H H n-C₃H₇ —

n²⁰ _(D) = 1.5522 28 CH₃ H H CH₃ —

m.p. 90° C. 29 CH₃ H H CH₃ —

m.p. 130° C. 30 CH₃ H H CH₃ —

m.p. 103° C. (S isomer) 31 CH₃ H H CH₃ —

m.p. 130° C. (R isomer) 32 CH₃ H H CH₃ —

n²⁰ _(D) = 1.5861 33 CH₃ H H CH₃ —

viscous 34 CH₃ H H CH₃ —

oil 35 CH₃ H H CH₃ —

n²⁰ _(D) = 1.5572 36 CH₃ H H CH₃ —

m.p. 131° C. 37 CH₃ H H C₂H₅ —

viscous 38 CH₃ H H CH₃ —

m.p. 68° C. 39 CH₃ H H C₂H₅ —

viscous 40 CH₃ H H CH₃ —

viscous 41 CH₃ H H CH₃ —

m.p. 72° C. 42 CH₃ H H C₂H₅ —

viscous 43 CH₃ H H C₂H₅ —CH₂O—

viscous 44 CH₃ H H CH₃ —

m.p. 108-10° C. 45 CH₃ H H CH₃ —

oil 46 CH₃ H H CH₃ —

m.p. 95° C. 47 CH₃ H H CH₃ —

m.p. 134° C. 48 CH₃ H H C₂H₅ —

m.p. 117° C. (R isomer) 49 CH₃ H H CH₃ —

m.p. 87° C. (R isomer) 50 CH₃ H H C₂H₅ —

m.p. 126° C. (S isomer) 51 CH₃ H H CH₃ —

m.p. 71° C. (S isomer) 52 CH₃ H H CH₃ —CH₂CH₂—

m.p. 87° C. 53 CH₃ H H CH₃ —CH₂CH₂—

m.p. 75° C. (R isomer) 54 CH₃ H H C₂H₅ —CH₂OCH₂—

oil 55 CH₃ H H C₂H₅ —CH₂OCH₂—

m.p. 83° C. 56 CH₃ H H C₂H₅ —CH₂OCH₂—

m.p. 95° C. 57 CH₃ H H C₂H₅ —CH₂OCH₂—

oil 58 CH₃ H H C₂H₅ —CH₂OCH₂—

m.p. 86° C. 59 CH₃ H H C₂H₅ —CH₂OCH₂—

oil 60 CH₃ H H C₂H₅ —CH₂OCH₂—

oil 61 CH₃ H H C₂H₅ —CH₂OCH₂—

oil 62 CH₃ H H C₂H₅ —CH₂OCH₂—

oil 63 CH₃ H H C₂H₅ —CH₂OCH₂—

oil 64 CH₃ H H C₂H₅ —CH₂OCH₂—

viscous 65 CH₃ H H C₂H₅ —CH₂OCH₂—

m.p. 79° C. 66 CH₃ H H H —CH₂SCH₂—

viscous 67 CH₃ H H H —

oil 68 CH₃ H H H —

oil 69 CH₃ CH₃ H H —

oil 70 CH₃ H H H —

m.p. 121° C. 71 CH₃ H H C₂H₅ —CH₂S—

m.p. 99-102° C. 72 CH₃ H H CH₃ —CH₂S—

oil 73 CH₃ H H CH₃ —CH₂S—

oil 74 CH₃ H H C₂H₅ —CH₂S—

oil 75 CH₃ H H C₂H₅ —CH₂S—

oil 76 CH₃ H H C₂H₅ —CH₂SCH₂—

oil 77 CH₃ H H C₂H₅ —CH₂S—

oil 78 CH₃ H H CH₃ —CH₂S—

m.p. 145° C. 79 CH₃ H H C₂H₅ —CH₂S—

oil 80 CH₃ H H C₂H₅ —CH₂S—

m.p. 135-38° C. 81 CH₃ H H C₂H₅ —CH₂S—

m.p. 240-43° C. 82 CH₃ H H C₂H₅ —CH₂S—

oil 83 CH₃ H H CH₃ —

m.p. 150° C. (S isomer) 84 CH₃ H H CH₃ —

m.p. 188° C. (S isomer) 85 CH₃ H H CH₃ —CH₂CH₂—

m.p. 126° C. (S isomer) 86 CH₃ H H CH₃ —

m.p. 152° C. 87 CH₃ H H C₂H₅ —CH₂O—

m.p. 114° C. 88 CH₃ H H C₂H₅ —CH₂O—

m.p. 118° C. 89 CH₃ H H C₂H₅ —CH₂O—

m.p. 110° C. 90 CH₃ H H C₂H₅ —CH₂O—

m.p. 104° C. 91 CH₃ H H C₂H₅ —CH₂O—

m.p. 125° C. 92 CH₃ H H C₂H₅ —CH₂O—

m.p. 118° C. 93 CH₃ H H C₂H₅ —CH₂O—

viscous 94 CH₃ H H C₂H₅ —CH₂O—

m.p. 125° C. 95 CH₃ H H C₂H₅ —CH₂O—

m.p. 114° C. 96 CH₃ H H H —

m.p. 168° C. 97 CH₃ H H H —

m.p. 150° C. 98 CH₃ H H H —

m.p. 159° C. 99 CH₃ H H H —

m.p. 145° C. 100 CH₃ H H H —

m.p. 145° C. 101 CH₃ H H H —

m.p. 167° C. 102 CH₃ CH₃ H H —

viscous 103 CH₃ H H H —

m.p. 151° C. 104 CH₃ H H H —

m.p. 113° C. 105 CH₃ H H H —

m.p. 106° C. 106 CH₃ H H H —

m.p. 114° C. 107 CH₃ H H H —

m.p. 192° C. 108 CH₃ CH₃ H H —

m.p. 124° C. 109 CH₃ H H H —

m.p. 125° C. 110 CH₃ H H H —

m.p. 92° C. 111 CH₃ H H H —

m.p. 112° C. 112 CH₃ H H H —

m.p. 111° C. 113 CH₃ H H H —

m.p. 130° C. 114 CH₃ CH₃ H H —

m.p. 108° C. 115 CH₃ H H H —

m.p. 166° C. 116 CH₃ H H H —

m.p. 118° C. 117 CH₃ H H H —

m.p. 112° C. 118 CH₃ H H H —

m.p. 165° C. 119 CH₃ H H H —

m.p. 164° C. 120 CH₃ H H H —

m.p. 144° C. 121 CH₃ H H H —

m.p. 164° C. 122 CH₃ H H H —

m.p. 160° C. 123 CH₃ H H H —

m.p. 119° C. 124 CH₃ H H H —

m.p. 174° C. 125 CH₃ H H H —

m.p. 140° C. 126 CH₃ H H H —

m.p. 148° C. 127 CH₃ H H H —

m.p. 147° C. 128 CH₃ H H H —

m.p. 154° C. 129 CH₃ H H H —

m.p. 134° C. 130 CH₃ H H C₃H₇-i —

m.p. 138° C. 131 CH₃ H CH₃ CH₃ —C≡C—

m.p. 117° C. 132 CH₃ H CH₃ CH₃ —C≡C—

m.p. 153° C. 133 CH₃ H CH₃ CH₃ —C≡C—

viscous 134 CH₃ H CH₃ CH₃ —C≡C—

m.p. 138° C. 135 CH₃ H CH₃ CH₃ —C≡C—

m.p. 122° C. 136 CH₃ H CH₃ H —

m.p. 90° C. 137 CH₃ H CH₃ H —

m.p. 110° C. (R isomer) 138 CH₃ H CH₃ H —

m.p. 134° C. (S isomer) 139 CH₃ H CH₃ H —

viscous 140 CH₃ H CH₃ H —

m.p. 131° C. (R isomer 141 CH₃ H CH₃ H —

viscous (S isomer) 142 CH₃ H C₂H₅ H —

viscous 143 CH₃ H C₃H₇-n H —

m.p. 86° C. 144 CH₃ H CH₃ H —

m.p. 156° C. 145 CH₃ H CH₃ H —

m.p. 131° C. 146 CH₃ H CH₃ H —

m.p. >250° C. 147 CH₃ H CH₃ H —

m.p. 105° C. 148 CH₃ H CH₃ H —

m.p. 115° C. 149 CH₃ H CH₃ H —

m.p. 110° C. 150 CH₃ H CH₃ H —

m.p. 135° C. 151 CH₃ H CH₃ H —

m.p. 140° C. 152 CH₃ H CH₃ H —CH₂CH₂—

m.p. 95° C. 153 CH₃ H CH₃ H —CH₂CH₂—

viscous 154 CH₃ H CH₃ H —CH₂CH₂—

viscous 155 CH₃ H H H —CH(CH₃)—

m.p. 96° C. 156 CH₃ H CH₃ H —CH(CH₃)CH₂—

viscous 157 CH₃ H CH₃ H —CH(CH₃)CH₂—

viscous 158 CH₃ H CH₃ H —CH(CH₃)CH₂—

m.p. 108° C. 159 CH₃ H CH₃ H —CH(CH₃)CH₂—

viscous 160 CH₃ H CH₃ H —CH(CH₃)CH₂—

m.p. 122° C. 161 CH₃ H CH₃ H —CH(CH₃)CH₂—

viscous 162 CH₃ H CH₃ H —CH(CH₃)CH₂—

m.p. 120° C. 163 CH₃ H CH₃ H —

m.p. 134° C. 164 CH₃ H CH₃ H —

viscous 165 CH₃ H H H —C(CH₃)═CH—

m.p. 79° C. 166 CH₃ H H H —C(CH₃)₂—

m.p. 169° C. 167 CH₃ H CH₃ H —CH₂C(CH₃)₂—

viscous 168 CH₃ H CH₃ H —

viscous 169 CH₃ H C₂H₅ H —CH₂—

viscous 170 CH₃ H CH₃ H —CH₂CH₂—

viscous 171 CH₃ H CH₃ H —CH₂—

m.p. 84° C. 172 CH₃ H H H —CH(CH₃)CH₂—

viscous 173 CH₃ H H H —CH(CH₃)CH₂—

viscous 174 CH₃ H CH₃ H —CH₂O—

viscous 175 CH₃ H CH₃ H —CH₂O—

viscous 176 CH₃ H CH₃ H —CH₂O—

m.p. 118° C. 177 CH₃ H CH₃ H —CH₂O—

viscous 178 CH₃ H CH₃ H

viscous 179 H H CH₃ CH₃ —CH₂CH₂—

m.p. 74° C. 180 H H CH₃ H —CH₂CH₂—

m.p. 76° C. 181 H H CH₃ H —CH₂CH₂—

viscous 182 H H CH₃ H —CH₂CH₂—

viscous 183 H H H H —CH(CH₃)—

viscous 184 H H CH₃ H —CH(CH₃)CH₂—

viscous 185 H H CH₃ CH₃ —C≡C—

m.p. 75° C. 186 H H CH₃ CH₃ —C≡C—

m.p. 114° C. 187 H H CH₃ CH₃ —C≡C—

m.p. 80° C. 188 H H CH₃ CH₃ —C≡C—

m.p. 100° C. 189 H H CH₃ CH₃ —C≡C—

viscous 190 H H CH₃ CH₃ —C≡C—

m.p. 104° C. 191 H H CH₃ H —

viscous 192 H H CH₃ H —

m.p. 66° C. (R isomer) 193 H H CH₃ H —

m.p. 68° C. (S isomer) 194 H H CH₃ H —

viscous 195 H H C₂H₅ H —

viscous 196 H H C₃H₇-n H —

viscous 197 H H CH₃ H —CH₂CH₂—

viscous 198 H H H H —CH(CH₃)CH₂—

m.p. 95° C. 199 H H CH₃ H —

m.p. 78° C. 200 H H H H —C(CH₃)₂—

m.p. 84° C. 201 H H CH₃ H —CH₂—C(CH₃)₂—

viscous 202 CH₃ H H H —CH₂—

m.p. 153° C. 203 CH₃ CH₃ H CH₃ —

log P (pH 2.3) 2.32 204 CH₃ H H CH₃

log P (pH 2.3) 1.63 205 CH₃ H H C₂H₅ —

m.p. 143° C. (S isomer) 206 CH₃ H H C₂H₅ —

m.p. 135° C. (R isomer) 207 CH₃ H H C₂H₅ —CH₂—CH₂—

wax 208 CH₃ H H CH₃ —

log P (pH 2.3) 1.71 (R isomer) 209 C₃H₇-n H H CH₃ —

oil 210 C₃H₇-n H H CH₃ —

m.p. 135° C. 211 H H H CH₃ —

oil (R isomer) 212 H H H CH₃ —

oil 213 H H H H —CH₂CH₂—

oil 214 H H H H

oil 215 H H H CH₃

oil 216 H H H CH₃ —

oil 217 H H H CH₃ —CH₂C(CH₃)₂—

oil 218 H H H CH₃ —CH₂CH₂—

oil 219 H H H CH₃ —CH(CH₃)CH₂

oil 220 H H CH₃ CH₃ —C• C—

oil 221 H H H CH₃ —

oil 222 H H H CH₃ —

oil 223 H H H CH₃ —

oil 224 H H H CH₃ —

oil 225 H H H CH₃ —

oil 226 H H H CH₃ —

oil 227 C₂H₅ H H CH₃ —

oil 228 C₂H₅ H H CH₃ —

m.p. 111° C. 229 C₂H₅ H H C₂H₅ —

oil 230 C₂H₅ H H C₃H₇-n —

oil 231 C₂H₅ H H CH₃ —

m.p. 109° C. 232 C₂H₅ H H CH₃ —

oil 233 C₂H₅ H H CH₃ —

m.p. 87° C. 234 C₂H₅ H H CH₃ —

m.p. 81° C. 235 C₂H₅ H H CH₃ —

oil 236 C₂H₅ H H CH₃ —

m.p. 163° C. 237 C₂H₅ H H CH₃ —

m.p. 115° C. 238 C₂H₅ H H CH₃ —

oil 239 C₂H₅ H H CH₃ —

oil 240 CH₃ H H H —CH₂—

m.p. 107° C. 241 CH₃ H H H —

m.p. 113° C. 242 CH₃ H H H —

m.p. 101° C. 243 CH₃ H H H —CH₂—

m.p. 138° C. 244 CH₃ H H H —CH₂CH₂—

m.p. 67° C. 245 CH₃ H H H —

oil 246 CH₃ H H H —

m.p. 86° C. 247 CH₃ H H H —

m.p. 132° C. 248 CH₃ H H H —CH₂

m.p. 133° C. 249 CH₃ H H CH₃ —CH₂O—

oil 250 H H CH₃ CH₃ —CH₂CH₂—

m.p. 107° C. 251 H H H CH₃ —CH(CH₃)CH₂—

oil 252 H H H CH₃ —CH(CH₃)CH₂—

oil 253 H H H H —CH(CH₃)CH₂—

oil 254 H H H CH₃ —CH₂O—

m.p. 126° C. 255 H H H CH₃ —CH₂O—

oil 256 H H H CH₃ —CH₂O—

oil 257 H H H CH₃ —CH₂O—

oil 258 H H H CH₃ —CH₂O—

m.p. 108° C. 259 H H H CH₃ —CH₂O—

m.p. 112° C. 260 C₃H₇-n H H CH₃ —

oil 261 H H H H —CH₂—

oil 262 H H H H —

oil 263 H H H H —

oil 264 H H H H —CH₂—

oil 265 H H H H —

m.p. 69° C. 266 H H H H —CH₂—

oil 267 H H H H —

m.p. 77° C. 268 CH₃ H H H —

m.p. 135° C. 269 CH₃ H H H —(CH₂)₃—

m.p. 106° C. 270 H H H H —(CH₂)₃—

oil 271 C₂H₅ H H CH₃ —

m.p. 136° C. ((+)-Isomer) 272 C₂H₅ H H CH₃

m.p. 125° C. ((−)-isomer) 273 C₃H₇-n H H CH₃

m.p. 79° C. 274 C₃H₇-n H H CH₃ —

m.p. 118° C. ((+)-isomer) 275 C₃H₇-n H H CH₃

m.p. 116° C. ((−)-isomer) 276 CH₃ H H C₂H₅ —CH₂OCH₂

oil 277 CH₃ H H C₂H₅ —CH₂OCH₂

oil 278 CH₃ H H C₂H₅ —CH₂OCH₂—

oil (R isomer) 279 CH₃ H H C₂H₅ —

m.p. 134° C. 280 CH₃ H H C₂H₅

m.p. 62° C. 281 CH₃ H H C₂H₅ —

wax (S isomer) 282 CH₃ H H C₂H₅ —

m.p. 134° C. (R isomer) 283 CH₃ H H C₂H₅

m.p. 98° C. (R isomer) 284 CH₃ H H C₂H₅ —

m.p. 98° C. (S isomer) 285 CH₃ H H C₂H₅ —

m.p. 103° C. (S isomer) 286 CH₃ H H C₂H₅ —

log P(pH 2.3) 2.05 (R isomer) 287 CH₃ H H CH₃

log P (pH 2.3) 1.93 (S isomer) 288 CH₃ H H CH₃ —

log P (pH 2.3) 1.71 (S isomer) 289 CH₃ H H CH₃ —

m.p. 148° C. (S isomer) 290 CH₃ H H CH₃

m.p. 139° C. (R isomer) 291 CH₃ H H C₂H₅

m.p. 134° C. 292 CH₃ H H C₂H₅

m.p. 113° C. (S isomer) 293 CH₃ H H CH₃ —

log P (pH 2.3) 1.94 (R isomer) 294 CH₃ H H C₂H₅ —

m.p. 118° C. (R isomer) 295 CH₃ H H CH₃ —

wax 296 CH₃ H H CH₃ —

m.p. 148° C. (S isomer) 297 CH₃ H H CH₃ —

log P (pH 2.3) 0.78 (R isomer) 298 CH₃ H H CH₃ —

m.p. 149° C. (R isomer) 299 CH₃ H H CH₃ —

m.p. 140° C. 300 CH₃ H H CH₃ —

m.p. 138° C. (S isomer) 301 CH₃ H H CH₃ —

m.p. 133° C. (R isomer) 302 CH₃ H H CH₃ —

m.p. 141° C. 303 CH₃ H H CH₃ —

m.p. 193° C. 304 CH₃ H H CH₃ —

m.p. 132° C. 305 CH₃ H H CH₃ —

m.p. 158° C. 306 CH₃ H H C₃H₇-i —

log P (pH 2.3) 2.58 307 CH₃ H H CH₃ —

m.p. 133° C. 308 CH₃ H H CH₃ —

m.p. 147° C. 309 CH₃ H H CH₃ —

m.p. 126° C. 310 CH₃ H H C₂H₅ —CH₂CH₂

wax 311 CH₃ H H CH₃ —

m.p. 133° C. 312 CH₃ H H CH₃ —

viscous 313 CH₃ H H CH₃ —

m.p. 136° C. 314 CH₃ H H CH₃ —CH₂CH₂—

315 C₂H₅ H H CH₃ —CH₂CH₂—

316 C₃H₇-n H H CH₃ —CH₂CH₂—

317 C₃H₇-i H H CH₃ —CH₂CH₂—

318 C₂H₅ H H C₂H₅ —CH₂CH₂—

319 C₃H₇-n H H C₂H₅ —CH₂CH₂—

320 C₃H₇-i H H C₂H₅ —CH₂CH₂—

TABLE B (Ic)

Ex. No. R¹ R² Y R⁷ Physical const. B1 CH₃ H —

m.p. 121° C. B2 H H —

m.p. 137° C. B3 CH₃ H —

m.p. 205° C. B4 C₃H₇-n H —

m.p. 128° C. B5 C₂H₅ H —

m.p. 136° C. B6 C₃H₇-n H —

m.p. 82° C. B7 C₂H₅ H —

m.p 148° C. B8 CH₃ H —

m.p. 181° C. B9 CH₃ H —

m.p. 151° C. (decomp.)  B10 CH₃ H —

m.p. 213° C.  B11 CH₃ H —

viscous  B12 CH₃ H —

m.p. 179° C. B13  CH₃ H —

m.p. 84° C.

USE EXAMPLES Example A Critical Concentration Test

Test nematode: Meloidogyne incognita Solvent: 4 parts by weight ofacetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted tothe desired concentration.

The preparation of active compound is intimately mixed with the soilwhich is contaminated with the test nematodes. The concentration of theactive compound in the preparation is here virtually unimportant, onlythe amount of active compound per volume unit of soil, which is statedin ppm (=mg/l), is decisive. The treated soil is filled into pots,lettuce is sown in and the pots are kept at a greenhouse temperature of25° C.

After three weeks, the roots of the lettuces are examined forinfestation by nematodes (root galls), and the efficacy of the activecompound in % is determined. The efficacy is 100% when infestation isavoided completely and 0% when the infestation level is just as high asin the control plants in untreated, but equally infested, soil.

In this test a kill of 100% was effected, for example, by the compoundof Preparation Example 1 at an exemplary active compound concentrationof 20 ppm.

What is claimed is:
 1. A compound of formula (Ib)

wherein R¹ represents (i) hydrogen; (ii) optionally halogen-, cyano-, orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl; (iii) C₃-C₆-cycloalkyl that isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group I;, consisting of halogen andC₁-C₄-alkyl; or (iv) phenyl that is mono- to trisubstituted by identicalor different substituents selected from the group consisting ofhydroxyl; amino; cyano; nitro; halogen; optionally hydroxyl-, cyano-, orhalogen-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino, ordi(C₁-C₄-alkyl)amino; optionally halogen-substitutedC₁-C₄-alkyl-carbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkyl-carbonyl-amino,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, or C₁-C₄-alkylsulphonyl;aminocarbonyl; aminothiocarbonyl; C₁-C₄-alkylaminocarbonyl;di(C₁C₄-alkyl)aminocarbonyl; aminosulphonyl; C₁-C₄-alkylaminosulphonyl;di(C₁-C₄-alkyl)aminosulphonyl; and phenyl, phenoxy, phenylthio,phenylsulphinyl, phenylsulphonyl, benzyl, or phenylamino, wherein eachsuch phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl,benzyl, or phenylamino is optionally substituted by one or morehydroxyl, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, orC₁-C₄-alkylsulphonyl, or by one or more C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, C₁-C₄-halogenoalkylthio,C₁-C₄-halogenoalkylsulphinyl, or C₁-C₄-halogenoalkylsulphonyl having 1to 5 identical or different halogen atoms selected from the seriesconsisting of chlorine, fluorine, and bromine, R² represents (i)hydrogen; (ii) optionally halogen-, cyano-, or C₁-C₄-alkoxy-substitutedC₁-C₄-alkyl; or (iii) C₃-C₆-cycloalkyl that is optionally mono- ortrisubstituted by identical or different substituents selected from thegroup consisting of halogen and C₁-C₄-alkyl, R⁴ and R⁵ independently ofone another represent (i) hydrogen; (ii) optionally halogen-, cyano-, orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl; or (iii) C₃-C₆-cycloalkyl that isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₁-C₄-alkyl, R⁶ represents (i) phenyl or naphthyl, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of cyano; nitro; amino;fluorine; chlorine; bromine; methyl; ethyl; n- or i-propyl; n-, i-, s-,or t-butyl; methoxy; ethoxy; n- or i-propoxy; trifluoromethyl;difluoromethyl; trifluoromethoxy; difluoromethoxy; trifluoromethylthio;methylamino; dimethylamino; acetyl; propionyl; methoxycarbonyl;ethoxycarbonyl; methylthio; methylsulphinyl; methylsulphonyl;methylaminocarbonyl; ethylaminocarbonyl; n- or i-propylaminocarbonyl;dimethylaminocarbonyl; diethylaminocarbonyl; optionally cyano-, nitro-,fluorine-, chlorine-, methyl-, methoxy-, methylthio-, methylsulphinyl-,methylsulphonyl-, trifluoromethyl-, trifluoromethoxy-,trifluoromethylthio-, trifluoromethylsulphinyl-, ortrifluoromethylsulphonyl-substituted phenyl, phenoxy, phenylthio,phenylsulphinyl, phenylsulphonyl, benzyl, or phenylamino; (ii)cyclopentane, or cyclohexane, each of which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, methyl, ethyl, i-propyl,methoxy, ethoxy, trifluoromethyl, and trifluoromethoxy; or (iii)heterocycles having the formulas

each of which is optionally mono- to pentasubstituted by identical ordifferent substituents selected from the group consisting of cyano;nitro; fluorine; chlorine; bromine; methyl; ethyl; n- or i-propyl;methoxy; trifluoromethyl; dimethylamino; phenyl that is optionallysubstituted with substituents selected from the group consisting ofcyano; nitro; amino; fluorine; chlorine; bromine; methyl; ethyl; n- ori-propyl; n-, i-, s-, or t-butyl; methoxy; ethoxy; n- or i-propoxy;trifluoromethyl; difluoromethyl; trifluoromethoxy; difluoromethoxy;trifluoromethylthio; methylamino; dimethylamino; acetyl; propionyl;methoxycarbonyl; ethoxycarbonyl; methylthio; methylsulphinyl;methylsulphonyl; methylaminocarbonyl; ethylaminocarbonyl; n- ori-propylaminocarbonyl; dimethylaminocarbonyl; diethylaminocarbonyl; andoptionally cyano-, nitro-, fluorine-, chlorine-, methyl-, methoxy-,methylthio-, methylsulphinyl-, methylsulphonyl-, trifluoromethyl-,trifluoromethoxy-, trifluoromethylthio-, trifluoromethylsulphinyl-, ortrifluoromethylsulphonyl-substituted phenyl, phenoxy, phenylthio,phenylsulphinyl, phenylsulphonyl, benzyl, or phenylamino, X represents(i) a single bond or (ii) a grouping selected from the group consistingof —CH₂—, —(CH₂)₂—, —(CH₂)₃—, —CH(CH₃)—, —C(CH₃)₂—, —CH₂C(CH₃)₂—,—CH(CH₃)CH₂—, —CH₂O—, —CH₂S—, —(CH₂)₂O—, —(CH₂)₂S—, —CH₂OCH₂—,—CH₂SCH₂—, —C(CH₃)═CH—, —C≡C—, —(CH₂)₃—N(CH₃)—, —(CH₂)₃—N(C₂H₅)—,—(CH₂)₃—N(CH₃)—CH₂—, and —(CH₂)₃—N(C₂H₅)—CH₂—.
 2. A compound of theformula (Ib) according to claim 1 wherein R¹ represents (i) hydrogen;(ii) optionally cyano-, fluorine, chlorine-, methoxy-, orethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, ort-butyl; (iii) cyclopropyl, cyclopentyl, or cyclohexyl, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl, and ethyl; or (iv) phenyl that is optionally mono- totrisubstituted by identical or different substituents selected from thegroup of cyano; nitro; amino; fluorine; chlorine; bromine; optionallyfluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-,s-, or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, ort-butoxy, methylamino, ethylamino, n- or i-propylamino, ordimethylamino; optionally fluorine- and/or chlorine-substituted acetyl,propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylthio, methylsulphinyl, methylsulphonyl, ethylthio, ethylsulphinyl,or ethylsulphonyl; aminocarbonyl; aminothiocarbonyl;methylaminocarbonyl; ethylaminocarbonyl; n- or i-propylaminocarbonyl;dimethylaminocarbonyl; diethylaminocarbonyl; aminosulphonyl;methylaminosulphonyl; ethylaminosulphonyl; dimethylaminosulphonyl;diethylaminosulphonyl; optionally cyano-, nitro-, fluorine-, chlorine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s-, or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl, n- ori-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- ori-propylsulphonyl-, difluoromethoxy-, trifluoromethoxy-,trifluoromethylthio-, trifluoromethylsulphinyl-, ortrifluoromethylsulphonyl-substituted phenyl, phenoxy, phenylthio,phenylsulphinyl, phenylsulphonyl, benzyl, or phenylamino, R² represents(i) hydrogen; (ii) optionally cyano-, fluorine-, chlorine-, methoxy-, orethoxy-substituted methyl, ethyl, n- or i-propyl and n-, i-, s-, ort-butyl; or (iii) cyclopropyl, cyclopentyl, or cyclohexyl, each or whichis optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl, and ethyl, and R⁴ and R⁵ independently of one anotherrepresent (i) hydrogen; (ii) optionally cyano-, fluorine-, chlorine-,methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-,i-, s-, or t-butyl; or (iii) cyclopropyl, cyclopentyl, or cyclohexyl,each of which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, and ethyl.
 3. A compound of the formula (KIb)according to claim 1 wherein R² represents hydrogen, methyl, ethyl, n-or i-propyl, or cyclopropyl.
 4. A process for preparing a compound ofthe formula (Ib) according to claim 1 comprising reacting a compound ofthe formula (II)

wherein R represents CN, R¹ is as defined for formula (Ib) of claim 1, Qrepresents oxygen or sulphur, and Z represents C₁-C₄-alkyl, with acompound of the formula (III)

wherein R² is as defined in claim 1, and R³ represents

wherein R⁴, R⁵, and R⁶ are each as defined for formula (Ib) of claim 1,in the presence of a diluent.
 5. A pesticide comprising one or more ofthe compounds of claim 1 and a member selected from the group consistingof liquid solvents, solid carriers, surfactants and mixtures thereof. 6.A process for preparing pesticides comprising mixing one or more of thecompounds of claim 1 with a member selected from the group consisting ofliquid solvents, solid carriers, surfactants and mixtures thereof.
 7. Amethod of controlling pests selected from the group consisting ofinsects, arachnids, nematodes and ectoparasites comprising allowing aneffective amount of one or more of the compounds of claim 1 to act onsaid pests and/or their habitat.